CHEMICAL MODIFICATION OF SPIRAMYCINS: V. SYNTHESIS AND ANTIBACTERIAL ACTIVITY OF 3'-OR 4'''-DE-N-METHYLSPIRAMYCIN I AND THEIR N-SUBSTITUTED DERIVATIVES

The 3'- and 4'''-de-N-methylspiramycins were synthesized selectively, and then were converted to various N-substituted derivatives. 4'''-De-N-methyl derivatives were more active than 3'-de-N-methyl ones. Among the derivatives, 4'''-N-Fmoc-glycyl...

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Bibliographic Details
Published in:Journal of antibiotics 1985, Vol.38(2), pp.186-196
Main Authors: SANO, HIROSHI, TANAKA, HARUO, YAMASHITA, KINYA, OKACHI, RYO, OMURA, SATOSHI
Format: Article
Language:English
Subjects:
Animals
Anti-Bacterial Agents - chemical synthesis
Anti-Bacterial Agents - pharmacology
Binding Sites
Carbohydrates. Nucleosides and nucleotides
Chemical Phenomena
Chemistry
Chromatography, High Pressure Liquid
Exact sciences and technology
Leucomycins
Magnetic Resonance Spectroscopy
Mice
Microbial Sensitivity Tests
Nucleosides, nucleotides and oligonucleotides
Organic chemistry
Preparations and properties
Ribosomes - metabolism
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Description
Summary:The 3'- and 4'''-de-N-methylspiramycins were synthesized selectively, and then were converted to various N-substituted derivatives. 4'''-De-N-methyl derivatives were more active than 3'-de-N-methyl ones. Among the derivatives, 4'''-N-Fmoc-glycyl and 4'''-N-benzyl-4'''-de-N-methylspiramycin I were the most active in vitro, and were comparable to spiramycin I. 4'''-De-N-methylspiramycin I was about half as active as spiramycin I in vivo.
ISSN:0021-8820
1881-1469
DOI:10.7164/antibiotics.38.186